There has always been a coveted, special role within startups and enterprises throughout Silicon Valley. Primarily driven by the status or caliber of the applicant (think ex-consultant from McKinsey, Bain or BCG, and MBA graduate of HBS, Stanford GSB or Wharton), these roles became highly respected in a short period of time. First come associate product manager/product managers roles, then jobs in business operations, and recently followed by the Chief of Staff position. But a new opportunity emerges in the wake of the rest: the founder-in-residence (FiR). A cousin of the canonically-known entrepreneur-in-residence (EiR) job, the major difference between the two is that FiR roles more frequently appear within early-stage startups, as opposed to EiRs in venture capital firms, universities, and startup accelerators. Gillian O’Brien, a FiR at Pilot, an early-stage company providing “finance, accounting, and tax services for startups and growing businesses,” shares her perspective on the new presence of FiRs within the tech ecosystem.
Frederick Daso: It’s clear that there is a definite progression of “it” roles within Silicon Valley, starting with the rise of the product manager role to the emerging focus on entrepreneurs-in-residences/founders-in-residence. However, upon further examination, would you say this shift is occurring based on the caliber of individuals chasing after it or the unique experience required for the role?
Gillian O’Brien: I think it’s both.
There’s been a startup boom happening over the last several years. From my perspective, starting a company has never been more accessible, with Y Combinator growing its cohort each year and new accelerators launching constantly.
I think two outcomes are created as a result:
More companies are being started. More people are stepping into the ring to be a founder. As this community grows, the need for products and services that support them grows. Take Pilot, for example. With more businesses starting, more founders are encountering the pain of bookkeeping (these unglamorous tasks are not usually part of the founder’s dream). Pilot specializes in providing finance, accounting, and tax services for startups, and thousands of startups are customers today. This creates a need for someone on Pilot’s side who understands that founder’s audience very well. While FIR/EIR is different at each institution, one through-line is that this person is leaned on for their understanding of the entrepreneurial community.
More companies are failing. I say this as a matter of math — more are failing because more are being started. And this creates a new kind of candidate: the ex-founder. Some people who start companies will never work for someone else, but some (like me) will. This type of candidate has a special type of experience they can lend to a business. And they have different goals than most other candidates — they want to start businesses again. The result is that what they can contribute to and what they crave out of their jobs is creating the need for a new kind of role.
Daso: Among these “it” roles, the Chief of Staff position is the most unique as it originated in government, and only one person can do it at a time. What did you learn from your time as a Chief of Staff that, combined primarily with your experience as a former founder, put you in a position to succeed in a Founder-In-Residence role?
O’Brien: When the company I founded didn’t work out, there were a few options on the table for what was next. I could start another business right away, work at a big company, or be an early employee somewhere.
Many people advised the big-co option, suggesting that going from one early-stage startup to the next with no break was a recipe for burnout.
Still, I chose the early employee path. I wanted to stay as close to the founder role as possible. Still, I felt I had a lot to learn before stepping up to that plate again. The Chief of Staff role was an opportunity to join in a generalist position as the 5th employee at a company not worlds further along than Cherry was when we closed doors. I was able to keep myself from straying away from the YC ethos and my founder roots.
I had learned a lot at Cherry about going from 0 to 1 — as Chief of Staff, I got to learn how to scale. Ultimately, it made me realize how passionate I am about startups and how much respect I have for founders. How much I want to be one again, eventually. I did end up burning out a little, but I had a lot of fun.
Daso: Given your previous experience as a co-founder of Cherry, what lessons did you learn that shaped your work as Pilot’s FIR?
O’Brien: As a first-time founder at Cherry, the biggest learning was just what being a founder is like. What’s shaping my work at Pilot today is drawing on that lived experience, which allowed me to understand what it’s all about — what you go through, how you feel.
There’s just no substitute for being a founder (if you don’t have the blood, sweat, and tears at home, store-bought is not fine).
The thrill of first users, the drudge of fundraising, the angst of discovering all of the un-glamorous work you now have to own (like bookkeeping, legal, hr), the punch-in-gut feeling of a customer churning, the exhaustion created by an investor ‘no,’ the relief and pride of a deal closed, the overwhelming sense of responsibility, the numbness of another all-nighter, the treadmill of growth and ever-moving goalposts. As a first-time founder, it was hard not to react emotionally to everything — but that intensity was my fuel.
Experiencing those highs and lows helped me connect to other founders and gave me a perspective that I can share with them. I’m not done with my founder journey and know I’ll be back in a founder’s shoes again one day, letting me stay in that headspace.
Daso: What kind of experience do ex-founders bring to the table for startups looking to hire them? How can startups get the best of ex-founders such as yourself in FIR roles?
O’Brien: Founders bring “zero to one” experience, which is always valuable to a startup. There are two components to this:
Founders think about how things could be versus accepting the way they are. As a company grows, people unconsciously become attached to the way things have been done until that point. So someone slow to accept the norms can be a needed nuisance if the company wants to be disruptive.
Beyond just thinking differently, founders have experience bringing their ideas to fruition, often with few resources. They’ve made prototypes and MVPs by themselves, with little engineering power and very little (or sometimes no) capital. They’ve been scrappy and acted quickly to capitalize on market opportunities. People can also become overly dependent on budgets or collaborators to accomplish things as a company grows. A founder won’t default to that, which can help the company move and learn faster.
To get the best out of an ex-founder, tell them about your pain points, and give them the room to invent and execute a solution.
However, founders can also over-index on being scrappy and inventive in a self-defeating way.
For example: quite often, founders will try to reinvent the wheel or hack aspects of their business like recruiting, accounting, and HR — either by habit or because they feel like, as a founder, they ‘should.’ If your business is one that’s focused on disrupting these specific areas, then, by all means, go against the grain. But otherwise, it’s a waste of time and creative energy to DIY-it or hack together cheap solutions to avoid walking in the footsteps of successful companies that came before yours. As a founder, you need to be decisive with your time and rigorous in how it’s spent.
In the context of Pilot’s product and services, I can use emotional maturity to help founders understand that it isn’t a good use of time and effort trying to do accounting, tax, and bookkeeping in a hack-y way. Pilot has already proven it does those things well for thousands of other startups.
Daso: What are some of the critical factors that first-time founders overlook when learning how to scale?
O’Brien: One critical thing that is overlooked as a founder learns to scale is whether or not they are scaling in the right direction. Cherry, for example, quickly grew from 0 to 24 customers within two or three months. But we later realized that we’d grown the wrong thing. We’d scaled our customer base, but we needed to build the wrong customers for the business. While the product we’d made had taken us this far, it became clear that it wouldn’t take us much further. We’d hit somewhat of a dead end. Similarly, companies with resources to deploy can end up scaling teams and product lines that are directionally off, and it ends up being a much more expensive mistake for them.
Daso: Given that a first-time founder can’t know these things in advance, would it make sense for early-stage startups to have FIR roles or consulting opportunities where ex-founders can provide stage-specific advice on generating and maintaining startup growth?
O’Brien: Founders are already surrounding themselves with other founders they admire, one or two steps ahead of them. They source investors, advisors, and coaches who have been in their shoes, who can share wisdom and point out blind spots. I think that this can also manifest itself as an FIR role if it’s what both parties want it to be called. This reminds me of something already in motion at On Deck, where operators with founder ambition are being matched to startups through an EiR program.
Because I’m an ex-founder and got caught in these traps myself, I can share that context with current founders, making the message more effective. They are usually eager to learn from someone else’s mistakes, and I’m happy to be open with what mine were.
Daso: What advice would you give to those seeking FIR roles as they grow in popularity?
O’Brien: Being an FIR in a company or other institution is different from being the founder of your own company. It’s good to be aware of that and not to ignore the new context you are operating in, but that said, you shouldn’t wait for permission to think or act like a founder in your role.
Like the advice I would give to incoming Chiefs of Staff, I think it’s good to begin the role with your own idea of who and where you want to be on the other side. If your personal goals align with those of the company, you can let them be your North Star and remain open to uncovering new pain points, perspectives, ideas, and solutions every day while the path unfolds itself.